Kevin is feeling pressure from the guys in the locker room to sleep with Winnie, since they have been going out for 6 years, it due time. Kevin seizes the opportunity to be along with Winnie when his parents take a trip out of town for one night, so he baits her into coming over to study for the SATs. She agrees, and even though Kevin creates a romantic atmosphere, Winnie wants to study, but then figures out Kevin's plan and informs him that girls have a "talk" too. Despite, his attempts at seduction, Kevin and Winnie end up doing what they always do--reminisce about their past together, as they watch a movie on TV. They wind up falling asleep together on the couch and have to rush to school so they can make it on time. After Winnie tells her parents where she was all night and they express how they trust him, Kevin feels frustrated. So much so that guys catch him in his mood and assume its about Winnie. Then Kevin makes the mistake of letting them get the wrong idea about him and Winnie and tells them to use their imagination of what happened, which they do, especially Kenny Steuben (Chance Quinn), who tells everyone. By lunch time, the whole school knows about their supposed actions, including an ashamed Winnie. Later, on his father's advice, Kevin goes to Winnie's house to apologize, but to his surprise, Winnie breaks up with him because what he's done is unfixable to her. She leaves Kevin to ponder his inexcusable actions at her doorstep. Guest starring Jason Horst as Jay.